A hydrosilylation reaction that combines a compound with a vinyl group and a compound with a silicon-bonded hydrogen atom by reacting them in the presence of a platinum catalyst is a reaction that is commonly used in the synthesis of organosilanes and organopolysiloxanes, as well as in the modification and silylation of organic compounds and organic polymers. It is known to produce halosilylated hydrocarbon compounds by causing a hydrosilylation reaction between a hydrocarbon compound having an aliphatic unsaturated bond and a hydrogenhalosilane.
It is known, that for the purposes of acceleration and control, such a reaction can be conducted in the presence of oxygen, unsaturated ketone, unsaturated alcohol, tertiary alcohol, ene-yne compound, acetylene alcohol, or acetylene ether (see, e.g. Japanese Unexamined Patent Application Publication [hereinafter referred to as Kokai] H5-213972, Kokai H6-234777, Kokai H8-208838, Kokai H8-231563, Kokai H8-291181, Kokai H9-25281, Kokai H10-29996).
However, the inventor has found that even though a hydrosilylation reaction is conducted between a diene-type compound having vinyl groups on both molecular terminals and a hydrogenhalosilane in the presence of the aforementioned compounds, it is difficult to produce chain hydrocarbons with halosilylated terminal carbon atoms quickly and with improved yield. This is because the process is accompanied by the inevitable formation of by-products in the form of halosilyl group position-changed isomers due to double bond transfer, i.e. by the formation of chain hydrocarbons halosilylated at carbon atoms other than its terminal carbon atoms.
Kokai H9-157276 and Kokai H9-192494 disclose a method wherein 3-chroloropropyltrichlorosilane is produced by subjecting allyl chloride and trichlorosilane to hydrosilylation in the presence of phosphine or tertiary amine. Kokai H11-80167 discloses a method wherein a terminal-silylated polymer is produced by subjecting a polymer with terminal allyl groups and a hydrogenchlorosilane, hydrogenalkoxysilane, or the like, to hydrosilylation in the presence of sulfur.
A disadvantage of the method based on the presence of phosphine or a tertiary amine is that it is unsuitable for selectively halosilylating carbon atoms on terminals of a compound that has vinyl groups on both terminals. A disadvantage of the method based on the presence of sulfur is that sulfur itself may significantly impair activity of a platinum catalyst, so that if it is added in an excessive amount, it will also impair the hydrosilylation reaction. On the other hand, it is not easy to adjust the amount of sulfur to be added to the reaction.
When the chain hydrocarbon halosilylated at its terminal carbon atoms in its initial form or in an alkoxysilylated form obtained by reacting it with an alcohol, is used as a coupling agent, surface-treating agent, or a starting material for modified silicones, it possesses better characteristics than the chain hydrocarbon halosilylated at carbon atoms other than its terminal carbon atoms. Therefore, a demand still exists for a method that would allow production of chain hydrocarbons halosilylated at its terminal carbon atom or its terminal carbon atoms, i.e., a chain hydrocarbon having a halosilyl group at its terminal carbon atom or halosilyl groups at its terminal carbon atoms with higher yield and speed.